3,5-Dichlorobenzoic acid → 3,5-Dichlorobenzoyl chloride

HRID 619976Notes

Reaction equation

HRID 619976 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:9](O)=[O:10]>N1C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:9]([Cl:3])=[O:10]

Participants

4

Reactant 2

HCID 58113,5-Dichlorobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 761913,5-Dichlorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

49.4 g of thionyl chloride and 0.21 g of pyridine were added to 20 g of 3,5-dichlorobenzoic acid and the mixture was refluxed for 20 hours. Excessive thionyl chloride was removed by distillation. Dry hexane was added to the residue and an insoluble matter was filtered out of the resulting solution and hexane was removed under reduced pressure. The remaining solution was crystallized. 3,5-Dichlorobenzoyl chloride was obtained quantitatively.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. customExcessive thionyl chloride was removed by distillation
  3. additionDry hexane was added to the residue
  4. filtrationan insoluble matter was filtered out of the resulting solution and hexane
  5. customwas removed under reduced pressure
  6. customThe remaining solution was crystallized

Sources & evidence

ORD record
ord-8df120c60446410182b22db2e53e1172
Source dataset
uspto-grants-1989_04
Patent number
US04818394

Reaction notes

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